ES2648513T3 - Procedimiento para la preparación de derivados de ácido ciclohexanopolicarboxílico con baja proporción de productos secundarios - Google Patents
Procedimiento para la preparación de derivados de ácido ciclohexanopolicarboxílico con baja proporción de productos secundarios Download PDFInfo
- Publication number
- ES2648513T3 ES2648513T3 ES13773238.4T ES13773238T ES2648513T3 ES 2648513 T3 ES2648513 T3 ES 2648513T3 ES 13773238 T ES13773238 T ES 13773238T ES 2648513 T3 ES2648513 T3 ES 2648513T3
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- Prior art keywords
- weight
- polycarboxylic acid
- particularly preferably
- derivative
- active metal
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- 239000002253 acid Substances 0.000 title claims abstract description 73
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims description 57
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 129
- 239000003054 catalyst Substances 0.000 claims abstract description 65
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 229910052751 metal Inorganic materials 0.000 claims abstract description 41
- 239000002184 metal Substances 0.000 claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000011148 porous material Substances 0.000 claims abstract description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000007789 gas Substances 0.000 claims abstract description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 14
- 230000035515 penetration Effects 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002459 porosimetry Methods 0.000 claims abstract description 9
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 8
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 8
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 8
- 239000010948 rhodium Substances 0.000 claims abstract description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 5
- 238000010924 continuous production Methods 0.000 claims abstract description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 description 44
- 238000005984 hydrogenation reaction Methods 0.000 description 42
- -1 aromatic carboxylic acids Chemical class 0.000 description 29
- 150000002148 esters Chemical class 0.000 description 27
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 14
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 10
- 238000007037 hydroformylation reaction Methods 0.000 description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 6
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 5
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical class CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 5
- 239000004806 diisononylester Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000004626 scanning electron microscopy Methods 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- VRZRVMXNGMZLDB-UHFFFAOYSA-N 3-ethylheptan-1-ol Chemical compound CCCCC(CC)CCO VRZRVMXNGMZLDB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004439 Isononyl alcohol Substances 0.000 description 3
- MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 description 3
- 238000004453 electron probe microanalysis Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- QNJAZNNWHWYOEO-UHFFFAOYSA-N 2-ethylheptan-1-ol Chemical compound CCCCCC(CC)CO QNJAZNNWHWYOEO-UHFFFAOYSA-N 0.000 description 2
- JSUXZEJWGVYJJG-UHFFFAOYSA-N 2-propylhexan-1-ol Chemical compound CCCCC(CO)CCC JSUXZEJWGVYJJG-UHFFFAOYSA-N 0.000 description 2
- MQQCUZGHANGGIT-UHFFFAOYSA-N 3,4,5-trimethylhexan-1-ol Chemical compound CC(C)C(C)C(C)CCO MQQCUZGHANGGIT-UHFFFAOYSA-N 0.000 description 2
- HBUKPSFSXBTFFW-UHFFFAOYSA-N 3,5-dimethylheptan-1-ol Chemical compound CCC(C)CC(C)CCO HBUKPSFSXBTFFW-UHFFFAOYSA-N 0.000 description 2
- DNHFCNDAPIMDKL-UHFFFAOYSA-N 3,6-dimethylheptan-1-ol Chemical compound CC(C)CCC(C)CCO DNHFCNDAPIMDKL-UHFFFAOYSA-N 0.000 description 2
- YCBDLDKYDMUESI-UHFFFAOYSA-N 3-ethyl-4-methylhexan-1-ol Chemical compound CCC(C)C(CC)CCO YCBDLDKYDMUESI-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- BMDLBCTXXXEROC-UHFFFAOYSA-N 4,5-dimethylheptan-1-ol Chemical compound CCC(C)C(C)CCCO BMDLBCTXXXEROC-UHFFFAOYSA-N 0.000 description 2
- MWWKESKJRHQWEF-UHFFFAOYSA-N 4-Methyloctan-1-ol Chemical compound CCCCC(C)CCCO MWWKESKJRHQWEF-UHFFFAOYSA-N 0.000 description 2
- WWRGKAMABZHMCN-UHFFFAOYSA-N 6-methyloctan-1-ol Chemical compound CCC(C)CCCCCO WWRGKAMABZHMCN-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000002923 metal particle Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 125000005624 silicic acid group Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005211 surface analysis Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- BKUSIKGSPSFQAC-RRKCRQDMSA-N 2'-deoxyinosine-5'-diphosphate Chemical compound O1[C@H](CO[P@@](O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(NC=NC2=O)=C2N=C1 BKUSIKGSPSFQAC-RRKCRQDMSA-N 0.000 description 1
- DAEAMCPYMQHGGW-UHFFFAOYSA-N 2,3-dimethylheptan-1-ol Chemical compound CCCCC(C)C(C)CO DAEAMCPYMQHGGW-UHFFFAOYSA-N 0.000 description 1
- ZEIZTVAKJXMCSQ-UHFFFAOYSA-N 2,5-dimethylheptan-1-ol Chemical compound CCC(C)CCC(C)CO ZEIZTVAKJXMCSQ-UHFFFAOYSA-N 0.000 description 1
- HGDVHRITTGWMJK-UHFFFAOYSA-N 2,6-dimethylheptan-2-ol Chemical compound CC(C)CCCC(C)(C)O HGDVHRITTGWMJK-UHFFFAOYSA-N 0.000 description 1
- NRZVENBFUFCASY-UHFFFAOYSA-N 2-ethyl-4-methylhexan-1-ol Chemical compound CCC(C)CC(CC)CO NRZVENBFUFCASY-UHFFFAOYSA-N 0.000 description 1
- IGVGCQGTEINVOH-UHFFFAOYSA-N 2-methyloctan-1-ol Chemical compound CCCCCCC(C)CO IGVGCQGTEINVOH-UHFFFAOYSA-N 0.000 description 1
- TZWSLANDWSEXRD-UHFFFAOYSA-N 3,4-dimethylheptan-1-ol Chemical compound CCCC(C)C(C)CCO TZWSLANDWSEXRD-UHFFFAOYSA-N 0.000 description 1
- CLFSZAMBOZSCOS-UHFFFAOYSA-N 3-methyloctan-1-ol Chemical compound CCCCCC(C)CCO CLFSZAMBOZSCOS-UHFFFAOYSA-N 0.000 description 1
- GCBXGQPBCBPHSP-UHFFFAOYSA-N 4,6-dimethylheptan-1-ol Chemical compound CC(C)CC(C)CCCO GCBXGQPBCBPHSP-UHFFFAOYSA-N 0.000 description 1
- KFIRGGRDLDDWMX-UHFFFAOYSA-N 4-ethyl-3-methylhexan-1-ol Chemical compound CCC(CC)C(C)CCO KFIRGGRDLDDWMX-UHFFFAOYSA-N 0.000 description 1
- BBVCCVAFLKQRMK-UHFFFAOYSA-N 4-ethyl-5-methylhexan-1-ol Chemical compound CCC(C(C)C)CCCO BBVCCVAFLKQRMK-UHFFFAOYSA-N 0.000 description 1
- JSRZLXKKHMYWLL-UHFFFAOYSA-N 5,6-dimethylheptan-1-ol Chemical compound CC(C)C(C)CCCCO JSRZLXKKHMYWLL-UHFFFAOYSA-N 0.000 description 1
- CGCDFYUPZXVGIX-UHFFFAOYSA-N 5-methyloctan-1-ol Chemical compound CCCC(C)CCCCO CGCDFYUPZXVGIX-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical class CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- MWRSABPHNREIIX-UHFFFAOYSA-N 9,9-dimethyldecan-1-ol Chemical compound CC(C)(C)CCCCCCCCO MWRSABPHNREIIX-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 101100055113 Caenorhabditis elegans aho-3 gene Proteins 0.000 description 1
- 102100035474 DNA polymerase kappa Human genes 0.000 description 1
- 101710108091 DNA polymerase kappa Proteins 0.000 description 1
- IJFPVINAQGWBRJ-UHFFFAOYSA-N Diisooctyl phthalate Chemical compound CC(C)CCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC(C)C IJFPVINAQGWBRJ-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000000441 X-ray spectroscopy Methods 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021486 amorphous silicon dioxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- DIMOQAGSNHTROK-UHFFFAOYSA-N bis(2-ethylhexyl) cyclohexane-1,2-dicarboxylate Chemical compound CCCCC(CC)COC(=O)C1CCCCC1C(=O)OCC(CC)CCCC DIMOQAGSNHTROK-UHFFFAOYSA-N 0.000 description 1
- GXRDMEGSBKPONF-UHFFFAOYSA-N bis(2-methyloctyl) benzene-1,2-dicarboxylate Chemical compound CCCCCCC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)CCCCCC GXRDMEGSBKPONF-UHFFFAOYSA-N 0.000 description 1
- MTYUOIVEVPTXFX-UHFFFAOYSA-N bis(2-propylheptyl) benzene-1,2-dicarboxylate Chemical compound CCCCCC(CCC)COC(=O)C1=CC=CC=C1C(=O)OCC(CCC)CCCCC MTYUOIVEVPTXFX-UHFFFAOYSA-N 0.000 description 1
- TUOSWEIWIXJUAU-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,1-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1(C(=O)OCCCCCCC(C)C)CCCCC1 TUOSWEIWIXJUAU-UHFFFAOYSA-N 0.000 description 1
- YKGYQYOQRGPFTO-UHFFFAOYSA-N bis(8-methylnonyl) hexanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC(C)C YKGYQYOQRGPFTO-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229910021488 crystalline silicon dioxide Inorganic materials 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- FUXJJBJXVZIIMV-UHFFFAOYSA-N dioctyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCC FUXJJBJXVZIIMV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Toys (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12187399.6A EP2716623A1 (de) | 2012-10-05 | 2012-10-05 | Verfahren zur Herstellung von Cyclohexanpolycarbonsäure-Derivaten mit geringem Nebenproduktanteil |
| EP12187399 | 2012-10-05 | ||
| PCT/EP2013/070667 WO2014053618A1 (de) | 2012-10-05 | 2013-10-04 | Verfahren zur herstellung von cyclohexanpolycarbonsäure-derivaten mit geringem nebenproduktanteil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2648513T3 true ES2648513T3 (es) | 2018-01-03 |
Family
ID=47022500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13773238.4T Active ES2648513T3 (es) | 2012-10-05 | 2013-10-04 | Procedimiento para la preparación de derivados de ácido ciclohexanopolicarboxílico con baja proporción de productos secundarios |
Country Status (8)
| Country | Link |
|---|---|
| EP (2) | EP2716623A1 (pl) |
| JP (1) | JP2016500665A (pl) |
| KR (1) | KR20150064740A (pl) |
| CN (1) | CN104822648B (pl) |
| ES (1) | ES2648513T3 (pl) |
| MY (1) | MY169248A (pl) |
| PL (1) | PL2903959T3 (pl) |
| WO (1) | WO2014053618A1 (pl) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101797220B1 (ko) * | 2015-08-27 | 2017-11-13 | 한화케미칼 주식회사 | 프탈레이트 화합물의 수소화 방법 |
| CN106554278B (zh) * | 2015-09-29 | 2019-05-21 | 湖南长岭石化科技开发有限公司 | 一种环己烷-1,2-二甲酸二元酯的制备方法 |
| JP2019531873A (ja) | 2016-08-18 | 2019-11-07 | ザ ユニバーシティ オブ シカゴＴｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｃｈｉｃａｇｏ | 高度に効率的な有機変換のための金属酸化物に支持された地球に豊富な金属の触媒 |
| CN106431913A (zh) * | 2016-08-28 | 2017-02-22 | 山东成泰化工有限公司 | 一种制备环己烷邻二甲酸二高碳醇酯的方法 |
| CN107774257B (zh) * | 2016-08-31 | 2020-11-27 | 湖南长岭石化科技开发有限公司 | 一种加氢催化剂及其应用以及一种环己烷-1,2-二甲酸二元酯的制备方法 |
| CN109790101A (zh) * | 2016-09-09 | 2019-05-21 | 埃克森美孚化学专利公司 | 邻苯二甲酸酯的氢化方法 |
| EP3931175B1 (de) | 2019-02-25 | 2024-04-10 | Basf Se | Verfahren zur aufarbeitung von benzolpolycarbonsäureestern und deren verwendung zur herstellung von cyclohexanpolycarbonsäureestern |
| CN114644551B (zh) * | 2020-12-18 | 2023-09-26 | 湖南长炼新材料科技股份公司 | 一种苯甲酸加氢反应方法 |
| CN112851920B (zh) * | 2020-12-31 | 2021-12-07 | 东胜化学(上海)有限公司 | 一种醇酸树脂及其制备方法 |
| CN115709064B (zh) * | 2021-08-23 | 2024-07-12 | 中国石油化工股份有限公司 | 蛋壳型催化剂及其制备方法和应用以及选择性加氢制备环己烷-1,2-二甲酸二酯的方法 |
| WO2024153687A1 (de) | 2023-01-19 | 2024-07-25 | Basf Se | Verfahren zur herstellung von 1,2-cyclohexandicarbonsäuredialkylestern |
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| GB721540A (en) | 1950-12-13 | 1955-01-05 | Standard Oil Dev Co | Improvements in or relating to iso-octyl alcohol |
| GB879803A (en) | 1959-03-04 | 1961-10-11 | Harold Newby | Improvements in the production of alcohols |
| US3027398A (en) | 1960-02-01 | 1962-03-27 | Du Pont | Process for preparing dimethyl 1, 4-cyclohexanedicarboxylate |
| US3091628A (en) | 1961-02-23 | 1963-05-28 | Exxon Research Engineering Co | Telomerization of alkoxy boron compounds |
| US3203998A (en) | 1963-02-06 | 1965-08-31 | Exxon Research Engineering Co | Selective hydrogenation |
| US3308086A (en) | 1963-08-30 | 1967-03-07 | Union Carbide Corp | Ethylene copolymers with vinyl esters plasticized with phosphate and carboxylic esters |
| GB1165309A (en) | 1968-07-12 | 1969-09-24 | Shell Int Research | Process for the preparation of Higher Aliphatic Alcohols |
| GB1320188A (en) | 1970-10-15 | 1973-06-13 | Exxon Research Engineering Co | Hydrogenolysis of substituted tetrahydropyrans |
| DE2823165A1 (de) | 1978-05-26 | 1979-11-29 | Bayer Ag | Verfahren zur herstellung von cycloaliphatischen carbonsaeureestern |
| JPS63146835A (ja) | 1986-12-11 | 1988-06-18 | Japan Tobacco Inc | ニトリルの還元によるアルコ−ルの製造方法 |
| DE3913835A1 (de) | 1989-04-27 | 1990-10-31 | Basf Ag | Katalysator fuer die hydrierung aliphatischer ungesaettigter verbindungen |
| GB9102513D0 (en) | 1991-02-06 | 1991-03-27 | Exxon Chemical Patents Inc | Hydrocarbon production |
| US5136108A (en) | 1991-09-13 | 1992-08-04 | Arco Chemical Technology, L.P. | Production of oxygenated fuel components |
| EP0597069B1 (fr) | 1992-05-26 | 1998-08-12 | Firmenich Sa | Procédé enzymatique pour la préparation de n-hexanal, 3-(Z)-hexén-1-al, ou 2-(E)-hexén-1-al, ou des alcools correspondants mettant en oeuvre une lipoxygénase de soja et une lyase de goyave |
| DE4228887A1 (de) | 1992-08-29 | 1994-03-03 | Basf Ag | Verfahren zur katalytischen Isomerisierung von â-Alkenolen |
| JP3106411B2 (ja) | 1992-12-21 | 2000-11-06 | 東和化成工業株式会社 | １，４−シクロヘキサンジカルボン酸の製造方法 |
| RU2059597C1 (ru) | 1993-04-22 | 1996-05-10 | Иркутский институт органической химии СО РАН | Способ получения 3-метил-1-бутин-3-ола |
| US5319129A (en) | 1993-06-15 | 1994-06-07 | Eastman Kodak Company | Preparation of dimethyl cyclohexanedicarboxylates |
| US5286898A (en) | 1993-06-15 | 1994-02-15 | Eastman Kodak Company | Low pressure process for the hydrogenation of dimethyl benzenedicarboxylates to the corresponding dimethyl cyclohexanedicarboxlates |
| US5399742A (en) * | 1993-06-15 | 1995-03-21 | Eastman Chemical Company | Low pressure process for the manufacture of cyclohexanedicarboxylate esters |
| US5510441A (en) | 1993-07-15 | 1996-04-23 | General Electric Company | Process for producing octamethyltrisiloxane |
| DE4330489A1 (de) | 1993-09-09 | 1995-03-16 | Hoechst Ag | Verfahren zur Hydroformylierung von Butadien-1,3 |
| DE4339713A1 (de) | 1993-11-22 | 1995-05-24 | Basf Ag | Verfahren zur Oligomerisierung von Olefinen zu hochlinearen Oligomeren und Katalysatoren dafür |
| DE4431528A1 (de) | 1994-09-03 | 1996-03-07 | Basf Ag | Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol |
| US5463143A (en) | 1994-11-07 | 1995-10-31 | Shell Oil Company | Process for the direct hydrogenation of wax esters |
| DE19624485A1 (de) | 1996-06-19 | 1998-01-02 | Basf Ag | Verfahren zur Hydrierung einer aromatischen Verbindung in Gegenwart eines geträgerten Rutheniumkatalysators |
| DE19624484A1 (de) | 1996-06-19 | 1998-01-02 | Basf Ag | Verfahren zur Hydrierung einer aromatischen Verbindung in Gegenwart eines geträgerten Rutheniumkatalysators |
| WO1998000383A1 (en) * | 1996-06-28 | 1998-01-08 | New Japan Chemical Co., Ltd. | Process for the preparation of cyclohexanedimethanol |
| GB9615089D0 (en) | 1996-07-18 | 1996-09-04 | Exxon Chemical Patents Inc | Esters and compositions comprising them |
| MY129474A (en) * | 1997-12-19 | 2007-04-30 | Basf Ag | Method for hydrogenating benzene polycarboxylic acids or derivatives thereof by using a catalyst containing macropores |
| JP2000319444A (ja) | 1999-05-14 | 2000-11-21 | Mitsubishi Chemicals Corp | 可塑剤用ｃ７アルコール組成物及びそれを用いたフタル酸ジエステル可塑剤組成物 |
| DE10146847A1 (de) | 2001-09-24 | 2003-04-24 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Polycarbonsäureestergemischen mit hohem trans-Anteil |
| DE10251311A1 (de) | 2001-11-07 | 2003-05-15 | Basf Ag | Verfahren zur integrierten Herstellung von 2-Ethylhexanol, 2-Ethylhexan-1,3-diol und 2,4-Diethyloctan-1,5-diol |
| EP1323700B1 (en) * | 2001-12-28 | 2007-08-22 | Mitsubishi Gas Chemical Company, Inc. | process for producing hydrogenated aromatic polycarboxylic acid and process for producing hydrogenated aromatic polycarboxylic anhydride |
| DE10205361A1 (de) | 2002-02-08 | 2003-08-21 | Basf Ag | Phosphorchelatverbindungen |
| DE10225565A1 (de) | 2002-06-10 | 2003-12-18 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
| DE10232868A1 (de) | 2002-07-19 | 2004-02-05 | Oxeno Olefinchemie Gmbh | Feinporiger Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
| GB0227087D0 (en) | 2002-11-20 | 2002-12-24 | Exxonmobil Chem Patents Inc | Hydrogenation of benzene polycarboxylic acids or derivatives thereof |
| DE102005028752A1 (de) * | 2005-06-22 | 2007-01-04 | Oxeno Olefinchemie Gmbh | Gemisch von Diisononylestern der 1,2-Cyclohexandicarbonsäure, Verfahren zu deren Herstellung und Verwendung dieser Gemische |
| US7632962B2 (en) * | 2006-04-26 | 2009-12-15 | Eastman Chemical Company | Hydrogenation process and catalysts |
| EP2316811B1 (en) * | 2008-07-23 | 2015-12-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing hydrogenated aromatic polycarboxylic acid |
| KR101833077B1 (ko) | 2009-12-15 | 2018-02-27 | 바스프 에스이 | 방향족 화합물의 수소화를 위한 촉매 및 방법 |
-
2012
- 2012-10-05 EP EP12187399.6A patent/EP2716623A1/de not_active Withdrawn
-
2013
- 2013-10-04 EP EP13773238.4A patent/EP2903959B1/de not_active Not-in-force
- 2013-10-04 KR KR1020157011228A patent/KR20150064740A/ko not_active Withdrawn
- 2013-10-04 PL PL13773238T patent/PL2903959T3/pl unknown
- 2013-10-04 WO PCT/EP2013/070667 patent/WO2014053618A1/de not_active Ceased
- 2013-10-04 JP JP2015535029A patent/JP2016500665A/ja active Pending
- 2013-10-04 MY MYPI2015000797A patent/MY169248A/en unknown
- 2013-10-04 CN CN201380062955.3A patent/CN104822648B/zh not_active Expired - Fee Related
- 2013-10-04 ES ES13773238.4T patent/ES2648513T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150064740A (ko) | 2015-06-11 |
| PL2903959T3 (pl) | 2018-01-31 |
| MY169248A (en) | 2019-03-19 |
| CN104822648B (zh) | 2016-11-09 |
| CN104822648A (zh) | 2015-08-05 |
| WO2014053618A1 (de) | 2014-04-10 |
| JP2016500665A (ja) | 2016-01-14 |
| EP2903959A1 (de) | 2015-08-12 |
| EP2716623A1 (de) | 2014-04-09 |
| EP2903959B1 (de) | 2017-08-23 |
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